The Tragic Legacy Of Billie Holiday: A Story Of Resistance And Resilience

In 1939, Billie Holiday rode the service elevator in a midtown Manhattan hotel on her way to sing on stage. Of course, the hotel had a front door, but Holiday wasn’t allowed to use it because she was Black. Little did she know this was just the beginning of the troubles that would follow her that night.

Holiday stuck to her setlist, including singing “Strange Fruit,” a hauntingly emotional song against lynching with lyrics like “Southern trees bear strange fruit / Blood on the leaves and blood at the root / Black bodies swinging in the southern breeze / Strange fruit hanging from the poplar trees.” Her self-described way of being able to “sing like an instrument” made the performance particularly effective.

But that night she received a warning from the Federal Bureau of Narcotics (FBN), a government agency which lasted from 1930 to 1968: She was never to sing the song again. The link between the song and the anti-drug agency may feel disjointed, except that FBN commissioner Harry Anslinger drew a direct correlation.

“To Harry Anslinger, Billie Holiday was like the symbol of everything that America had to be afraid of,” Johann Hari, who wrote the book Chasing the Scream: The First and Last Days of the War on Drugs, told WNYC. “She had a heroin addiction because she’d been chronically raped as a child and she was trying to deal with the grief and the pain of that. And also, she was resisting white supremacy. And when she insisted on continuing on her right as an American citizen to sing ‘Strange Fruit,’ Anslinger resolves to destroy her.”

Anslinger: The Face of Racism in the War on Drugs

Harry Anslinger was known as an “extreme racist in the 1920s.” When he took on the role in the new agency that was part of the Treasury Department, he was determined to “eradicate all drugs, everywhere.” He had previously been part of the Department of Prohibition, but since the prohibition had been abolished, he was more determined than ever to take a strict stance on drugs.

Among his misguided strategies was his belief that jazz music was a part of the problem. He wrote memos claiming that jazz sounded like “the jungles in the dead of night” and that its songs “reek of filth.” His agents reported that “many among the jazzmen think they are playing magnificently when under the influence of marijuana, but they are actually becoming hopelessly confused and playing horribly.”

Anslinger's targeting of jazz music stemmed from his deep-seated biases. “You have to understand that he was regarded as an extreme racist in the 1920s,” Hari explained. “He used the N word so often in official memos that his own senators said he should have to resign.”

The Political Climate and Holiday's Courage

The controversial nature of “Strange Fruit” provided Anslinger with an excuse to target Holiday. “This was not a time when there were political pop songs,” Hari noted. “And to have an African American woman standing in front of a white audience singing a song against white supremacy and its violence was viscerally shocking at that moment.” Coupled with Holiday’s known struggles with addiction, Anslinger became laser-focused on taking her down.

Despite the risks, Holiday continued to perform “Strange Fruit,” embodying courage in her resistance against racism and injustice. Farah Jasmine Griffin of Columbia University’s African American and African Diaspora Studies remarked, “The kind of courage not only that she would risk her career but that she actually risked her life and her freedom because she felt that she had to sing this song.”

This act of defiance not only showcased her talent but also highlighted her resolve against the societal issues of her time. Billie Holiday’s music became a powerful statement against oppression, and her legacy continues to inspire artists and activists today.

The Pursuit of Holiday by Anslinger and His Agents

Anslinger, despite his aversion to hiring Black agents, assigned Jimmy Fletcher to investigate Holiday because of her Harlem base. Fletcher believed, “You victimize yourself by becoming a junkie,” which made him seem like the right fit for the job.

As Fletcher frequented Holiday’s neighborhood, he witnessed her struggles with addiction firsthand. However, their relationship grew complicated as they spent time together, even dancing at Club Ebony. Fletcher later expressed, “I had so many close conversations with her, about so many things,” hinting at the emotional connection they developed.

This connection complicated Fletcher's role as an undercover agent, as he navigated his feelings for Holiday amidst his duty to fulfill Anslinger’s agenda. Their bond became a tragic element in the story of Holiday’s life, showcasing the personal struggles intertwined with the political machinations of the time.

The Devastating Impact of Betrayal

Holiday's personal life was filled with turmoil, particularly with her husband, Louis McKay, who became enraged and ultimately worked with the FBN to set her up. After enduring physical abuse, she distanced herself from him, but McKay’s anger led to her downfall. He met with Anslinger in Washington, D.C., and they conspired to entrap Holiday.

Once caught, Holiday faced a trial that felt more like a personal vendetta than a legal proceeding. She wrote in her autobiography that the case felt like “The United States of America versus Billie Holiday.” Despite her pleas for help in recovering from her addiction, she was sentenced to a year in prison.

Even after her release, her license to perform was revoked, but she persevered, showcasing her resilience. Shortly after, she performed at Carnegie Hall, defying the odds stacked against her.

Enduring the Fight Against Addiction and Injustice

Anslinger was not finished with Holiday. He enlisted Col. George White, infamous for infiltrating a Chinese drug gang, to further target her. When White busted Holiday at a hotel, he claimed to find drugs in her possession, though many historians believe he planted them.

This act shattered Holiday again, forcing her back into addiction and derailing her career. Yet she continued to perform, maintaining her commitment to “Strange Fruit.” Her bravery in the face of adversity became a hallmark of her legacy.

The Final Years of Billie Holiday's Life

In 1959, after collapsing due to liver disease, Holiday found herself in a hospital bed, fearful that Anslinger’s pursuit was far from over. Her concerns were validated when Anslinger’s agents arrested her in the hospital, a move that devastated her spirit and highlighted the monstrous lengths to which he would go.

Protests erupted outside the hospital, with people pleading for her freedom. However, after ten days, her methadone treatment was cut off on Anslinger’s orders, leading to her tragic demise on July 17, 1959.

Anslinger’s satisfaction over Holiday’s death revealed the deep-rooted racism and cruelty that fueled his actions. His legacy of discrimination against marginalized artists and communities stands as a stark reminder of the injustices faced by many throughout history.

Remembering Billie Holiday's Legacy

While Billie Holiday's life ended tragically, her legacy of resilience and defiance lives on. Her artistry and courage in the face of systemic oppression remind us of the importance of standing up against injustice today. Farah Jasmine Griffin stated, “They aren’t going to get the hit that Billie Holiday got. They aren’t going to go to prison because they sang a song, right?”

As we reflect on her life, it’s essential to honor the sacrifices she made for her music and the profound messages embedded within her songs. Holiday’s spirit continues to inspire those who fight for equality and justice, ensuring that her voice is never forgotten.